Metallo‐Foldamers with Backbone‐Coordinative Oxime Peptides: Control of Secondary Structures

Metal-ligand coordination is akey interaction in the self-assembly of both biopolymers and synthetic oligomers. Although the binding of metal ions to synthetic proteins and peptides is knownt oy ield high-order structures,t he selfassembly of peptidomimetic molecules upon metal binding is still challenging. Herein we explore the self-assembly of three peptoid trimers bearing abipyridine ligand at their C-terminus, abenzyl group at their N-terminus,and apolar group (N-ethyl-R) in the middle position (R = OH, OCH 3 ,orNH 2 )upon Cu 2+ coordination. X-ray diffraction analysis revealed unique, highly symmetric,d inuclear cyclic structure or aqua-bridged dinuclear double-stranded peptoid helicates,f ormed by the self-assembly of two peptoid molecules with two Cu 2+ ions. Only the macrocycle with the highest number of intermolecular hydrogen bonds is stable in solution, while the other two disassemble to their corresponding monometallic complexes.

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Self‐Assembled Cyclic Structures from Copper(II) Peptoids

Ghosh

Fridman

Kosa

et al. 2018

Angewandte Chemie

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Cyclic Heterometallic Interactions formed from a Flexible Tripeptide Complex Showing Effective Antiferromagnetic Spin Coupling

et al. 2021

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Developing tunable motifs for heterometallic interactions should be beneficial for fabricating functional materials based on cooperative electronic communications between metal centers. Reported here is the efficient formation of cyclic heterometallic interactions from a complex containing an artificial tripeptide with metal binding sites on its main chain and side chains. X-ray structural analysis and X-ray absorption spectroscopy revealed that the cyclic metal-metal arrangements arise from the amide groups connecting four squareplanar Cu II centers and four octahedral Ni II centers in a cyclic manner. UV/Vis spectral studies suggested that this efficient formation was achieved by the selective formation of the square-planar Cu II centers and a crystallization process. Magnetic measurements using SQUID clarified that the cyclic complex represented the S = 2 spin state at low temperatures due to effective antiferromagnetic interactions between the Ni II and Cu II centers. Figure 1. Conceptual Figure showing the formation of the cyclic Cu II-Ni II arrangement using a flexible peptide ligand.

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Discrete Self‐Assembled Metallo‐Foldamers with Heteroleptic Sequence Specificity

Preston

2021

Angewandte Chemie

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Discrete and structurally diverse foldamer sequences are constructed in both natural and abiotic systems primarily using inert connectivity with irreversible organic covalent bonds, serving to preserve the identity of the sequence. The formation of sequences under thermodynamic control using labile coordination bonds would be attractive for synthetic ease and modular capability, but this presents issues regarding sequence preservation. Here is presented an approach integrating palladium(II) metal ions into the sequence itself, with fidelity maintained through use of complementary pairings of ligand arrangements at the metal centre. This is accomplished using sites of different denticity and/or hydrogen bonding capability. In this fashion, discrete and ordered metallo‐sequences are formed as thermodynamic products in a single step, and these then fold into defined conformations due to π–π interactions between electron‐rich and ‐poor aromatic regions of the combined componentry.

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Metallo‐Foldamers with Backbone‐Coordinative Oxime Peptides: Control of Secondary Structures

Cited by 9 publications

References 77 publications

Self‐Assembled Cyclic Structures from Copper(II) Peptoids

Self‐Assembled Cyclic Structures from Copper(II) Peptoids

Cyclic Heterometallic Interactions formed from a Flexible Tripeptide Complex Showing Effective Antiferromagnetic Spin Coupling

Discrete Self‐Assembled Metallo‐Foldamers with Heteroleptic Sequence Specificity

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